Field of the Invention
The present invention relates to hyrazine derivatives represented by the following general formula (I) and agricultural and horticultural insecticides: ##STR2## wherein Ar.sup.1 and Ar.sup.2, which may be the same or different, are unsubstituted phenyl groups; substituted phenyl groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; unsubstituted 5- or 6-membered heteroaryl groups having 1 to 3 heteroatoms which may be the same or different and are selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom; or substituted 5- or 6-membered heteroaryl groups which are the same as the above unsubstituted 5- or 6-membered heteroaryl groups, except for having as the substituent(s) one or more halogen atoms or (C.sub.1-6)alkyl groups, which may be the same or different, R.sup.1 is a hydrogen atom, a (C.sub.1-6)alkyl group, a (C.sub.2-6)alkenyl group or a (C.sub.2-6)alkynyl group, A is ##STR3## [wherein R.sup.2 is a hydrogen atom, a (C.sub.1-6)alkyl group, a (C.sub.2-6)alkenyl group or a (C.sub.2-6)alkynyl group, B is an unsubstituted and linear or branched (C.sub.1-6)alkylene group, a substituted and linear or branched (C.sub.1-6)alkylene group having one or more halogen atoms or (C.sub.1-6)alkoxy groups as the substituent(s), an unsubstituted and linear or branched (C.sub.2-6)alkenylene group, a substituted and linear or branched (C.sub.2-6)alkenylene group having one or more halogen atoms or (C.sub.1-6)alkoxy groups as the substituent(s), an unsubstituted and linear or branched (C.sub.2-6)alkynylene group, or a substituted and linear or branched (C.sub.2-6)alkynylene group having one or more halogen atoms or (C.sub.1-6)alkoxy groups as the substituent(s), the branched alkylene, alkenylene or alkynylene group being able to form a ring having 3 to 7 carbon atoms by bonding of substituents on the same carbon atom to each other, n is zero or 1, Q is a cyano group; a nitro group; a (C.sub.2-6)alkenyl group; a (C.sub.2-6)alkynyl group; an unsubstituted phenyl(C.sub.2-6)alkenyl group; a substituted phenyl(C.sub.2-6)alkenyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; an unsubstituted phenyl(C.sub.2-6)alkynyl group; a substituted phenyl(C.sub.2-6)alkynyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; a (C.sub.2-6)alkynyl(C.sub.2-6)alkenyl group; a (C.sub.2-6)alkenyl(C.sub.2-6)alkynyl group; EQU --OR.sup.3
(wherein R.sup.3 is a hydrogen atom; a (C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkyl group; a (C.sub.1-6)alkoxy(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylthio(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylsulfinyl(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylsulfonyl(C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkylthio(C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkylsulfinyl(C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkylsulfonyl(C.sub.1-6)alkyl group; a cyano(C.sub.1-6)alkyl group; a (C.sub.3-6)cycloalkyl group; a (C.sub.3-6)cycloalkyl(C.sub.1-6)alkyl group; a (C.sub.1-6)alkoxycarbonyl(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylcarbonyl(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylcarbonyl group; an unsubstituted amino(C.sub.1-6)alkyl group; a substituted amino(C.sub.1-6)alkyl group having one or two substituents which may be the same or different and are selected from the group consisting of (C.sub.1-6)alkyl groups and (C.sub.1-6)alkylcarbonyl groups; an unsubstituted carbamoyl(C.sub.1-6)alkyl group; a substituted carbamoyl(C.sub.1-6)alkyl group having one or two substituents which may be the same or different and are selected from (C.sub.1-6)alkyl groups; an unsubstituted phenyl group; a substituted phenyl group having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; an unsubstituted phenyl(C.sub.1-6)alkyl group; a substituted phenyl(C.sub.1-6)alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; an unsubstituted phenyl(C.sub.2-6)alkenyl group; a substituted phenyl(C.sub.2-6)alkenyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; an unsubstituted phenyl(C.sub.2-6)alkynyl group; a substituted phenyl(C.sub.2-6)alkynyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; a 5- or 6-membered heteroaryl group having 1 to 3 heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a 5- or 6-membered heteroaryl(C.sub.1-6)alkyl group having 1 to 3 heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom); ##STR4## (wherein R.sup.3 is as defined above, and m is zero, 1 or 2); EQU --COOR.sup.4
(wherein R.sup.4 is a hydrogen atom, a (C.sub.1-6)alkyl group, a halo(C.sub.1-6)alkyl group, a (C.sub.2-6)alkenyl group, a halo(C.sub.2-6)alkenyl group, a (C.sub.2-6)alkynyl group or a halo(C.sub.2-6)alkynyl group); ##STR5## (wherein R.sup.4 is as defined above); EQU --CON(R.sup.5)R.sup.6
(wherein R.sup.5 is a hydrogen atom; a (C.sub.1-6)alkyl group; a (C.sub.2-6)alkenyl group; a (C.sub.2-6)alkynyl group; an unsubstituted phenyl group; or a substituted phenyl group having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups, and R.sup.6 is a hydrogen atom; a (C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkyl group; a (C.sub.2-6)alkenyl group; a (C.sub.2-6)alkynyl group; a (C.sub.1-6)alkoxy(C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkoxy(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylthio(C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkylthio(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylsulfinyl(C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkylsulfinyl(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylsulfonyl(C.sub.1-6)alkyl group; a halo(C.sub.1-6)alkylsulfonyl(C.sub.1-6)alkyl group; a cyano(C.sub.1-6)alkyl group; a hydroxy(C.sub.1-6)alkyl group; a (C.sub.3-6)cycloalkyl group; a (C.sub.3-6)cycloalkyl(C.sub.1-6)alkyl group; a (C.sub.1-6)alkoxycarbonyl(C.sub.1-6)alkyl group; a (C.sub.1-6)alkylcarbonyl(C.sub.1-6)alkyl group; a carbamoyl(C.sub.1-6)alkyl group; a substituted carbamoylalkyl group having one or two substituents which may be the same or different and are selected from (C.sub.1-6)alkyl groups; an unsubstituted amino(C.sub.1-6)alkyl group; a substituted amino(C.sub.1-6)alkyl group having one or two substituents which may be the same or different and are selected from the group consisting of (C.sub.1-6)alkyl groups and (C.sub.1-6)alkylcarbonyl groups; or a 5- or 6-membered heteroaryl(C.sub.1-6)alkyl group having 1 to 3 heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R.sup.5 and R.sup.6 being able to be taken together to represent a (C.sub.4-6)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, --O--, --(SO).sub.m -- (wherein m is as defined above), or --N(R.sup.7)-- (wherein R.sup.7 has the meaning described below), and said alkylene group being able to have one or more substituents which may be the same or different and are selected from the group consisting of (C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxycarbonyl groups and phenyl group); EQU --SO.sub.2 N(R.sup.5)(R.sup.6)
(wherein R.sup.5 and R.sup.6 are as defined above); EQU --N(R.sup.7)R.sup.8
(wherein R.sup.7 and R.sup.8, which may be the same or different, are hydrogen atoms; formyl groups; cyano groups; (C.sub.1-6)alkyl groups; (C.sub.2-6)alkenyl groups; (C.sub.2-6)alkynyl groups; (C.sub.1-6)alkylcarbonyl groups; halo(C.sub.1-6)alkylcarbonyl groups; (C.sub.1-6)alkoxycarbonyl groups; halo(C.sub.1-6)alkoxycarbonyl groups; (C.sub.3-6)cycloalkylcarbonyl group; phenoxycarbonyl groups; (C.sub.1-6)alkylsulfonyl groups; unsubstituted carbamoyl groups; substituted carbamoyl groups having as the substituent(s) one or two (C.sub.1-6)alkyl groups which may be the same or different; unsubstituted carbamoyl(C.sub.1-6)alkyl groups; substituted carbamoyl(C.sub.1-6)alkyl groups having as the substituent(s) one or two (C.sub.1-6)alkyl groups which may be the same or different; unsubstituted thiocarbamoyl groups; substituted thiocarbamoyl groups having as the substituent(s) one or two (C.sub.1-6)alkyl groups which may be the same or different; unsubstituted sulfamoyl groups; substituted sulfamoyl groups having as the substituent(s) one or two (C.sub.1-6)alkyl groups which may be the same or different; unsubstituted (C.sub.1-6)alkoxycarboimidoyl groups; substituted (C.sub.1-6)alkoxycarboimidoyl groups having (C.sub.1-6)alkyl group as the substituent; unsubstituted (C.sub.1-6)alkylthiocarboimidoyl groups; substituted (C.sub.1-6)alkylthiocarboimidoyl groups having (C.sub.1-6)alkyl group as the substituent; unsubstituted phenyl groups; substituted phenyl groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; unsubstituted phenyl(C.sub.1-6)alkyl groups; substituted phenyl(C.sub.1-6)alkyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; unsubstituted phenylcarbamoyl groups; substituted phenylcarbamoyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; unsubstituted phenylcarbonyl groups; substituted phenylcarbonyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups; unsubstituted phenylsulfonyl groups; or substituted phenylsulfonyl groups having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups, halo(C.sub.1-6)alkylthio groups, (C.sub.1-6)alkylsulfinyl groups, halo(C.sub.1-6)alkylsulfinyl groups, (C.sub.1-6)alkylsulfonyl groups, halo(C.sub.1-6)alkylsulfonyl groups, (C.sub.1-6)alkoxycarbonyl groups, unsubstituted phenoxy group, substituted phenoxy groups having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, unsubstituted pyridyloxy group, substituted pyridyloxy groups having 1 to 4 substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C.sub.1-6)alkyl groups and halo(C.sub.1-6)alkyl groups, dioxy(C.sub.1-3)alkylene groups, and dioxyhalo(C.sub.1-3)alkylene groups); EQU --C(R.sup.9).dbd.NOR.sup.4
(wherein R.sup.4 is as defined above, and R.sup.9 is a hydrogen atom, a (C.sub.1-6)alkyl group, a halo(C.sub.1-6)alkyl group, an unsubstituted phenyl group, or a substituted phenyl group having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups and halo(C.sub.1-6)alkylthio groups); EQU --C(R.sup.9).dbd.N--N(R.sup.7)(R.sup.8)
(wherein R.sup.7, R.sup.8 and R.sup.9 are as defined above); or EQU --O--N.dbd.C(R.sup.9)(R.sup.10)
(wherein R.sup.9 is as defined above, and R.sup.10 is a hydrogen atom, a (C.sub.1-6)alkyl group, a halo(C.sub.1-6)alkyl group, an unsubstituted phenyl group, or a substituted phenyl group having 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C.sub.1-6)alkyl groups, halo(C.sub.1-6)alkyl groups, (C.sub.1-6)alkoxy groups, halo(C.sub.1-6)alkoxy groups, (C.sub.1-6)alkylthio groups and halo(C.sub.1-6)alkylthio groups)], ##STR6## [wherein R.sup.2, B, Q and n are as defined above], ##STR7## [wherein R.sup.2, B, Q and n are as defined above], or ##STR8## [wherein R.sup.2, B, Q and n are as defined above], and W is an oxygen atom or a sulfur atom. More particularly, the hydrazine derivatives of the general formula (I) of the present invention include hydrazine derivatives represented by the following general formulas (I-1), (I-2), (I-3) and (I-4). ##STR9## wherein Ar.sup.1, Ar.sup.2, R.sup.1, R.sup.2, B, n, Q and W are as defined above.
In the definition of the hydrazine derivatives of the general formula (I) of the present invention, the term "(C.sub.1-6)alkyl group", for example, means a linear or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl or the like. The prefix "halo" is used for expressing that a group has as its substituent(s) one or more halogen atoms which may be the same or different and are selected from chlorine, bromine, iodine and fluorine atoms. The term "haloalkyl group" means a substituted alkyl group having as the substituent(s) one or more halogen atoms which may be the same or different and are selected from the group consisting of chlorine atom, bromine atom, iodine atom and fluorine atom. The term "heteroaryl" in "heteroaryl group" or "heteroarylalkyl group" means a 5- to 6-membered ring having 1 to 3 heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, hydrogen atom and nitrogen atom, for example, heterocyclic groups such as furyl group, thienyl group, oxazole group, thiazole group, pyrazole group, imidazole group, pyridine group, etc.
The hydrazine derivatives of the general formulas (I-1) and (I-3) of the present invention have geometrical isomers, i.e., E-form and Z-form. The present invention also includes the E-form, the Z-form, and mixtures thereof. The hydrazine derivatives of the general formulas (I-2) and (I-4) have optical isomers, i.e., R-form and S-form. The present invention also includes the R-form, the S-form, and mixtures thereof.
Of the hydrazine derivatives of the general formula (I), compounds having a preferable structure are the hydrazine derivatives of the general formula (I-1). As the substituents of the hydrazine derivatives of the general formula (I-1), Ar.sup.1 and Ar.sup.2 are preferably unsubstituted phenyl groups or substituted phenyl groups having 1 to 3 substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, alkyl groups, haloalkyl groups, alkoxy groups and haloalkoxy groups. R.sup.1 and R.sup.2, which may be the same or different, are preferably hydrogen atoms, or methyl groups. B is preferably a methylene, a ethylene or a propylene group, or n is preferably zero.
Q is preferably a substituent such as cyano group, --OR.sup.3, --S(O).sub.m R.sup.3, --COOR.sup.4, --CON(R.sup.5)(R.sup.6), or N(R.sup.7)(R.sup.8).